HCID 131727291, compound → HCID 131727290, compound

HRID 1727310Notes

Reaction equation

HRID 1727310 reaction equation
C([NH:8][C:9]([NH:11][C:12]1([CH2:33][O:34][SiH3:35])[C:15]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:14]([C:28]([CH3:31])([CH3:30])[CH3:29])[CH:13]1[F:32])=[O:10])C1C=CC=CC=1>CC(O)=O.[Pd]>[C:28]([CH:14]1[C:15]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:12]([CH2:33][O:34][SiH3:35])([NH:11][C:9](=[O:10])[NH2:8])[CH:13]1[F:32])([CH3:31])([CH3:29])[CH3:30]

Participants

4

Reactant 1

HCID 131727291HCID 131727291, compound

Product 1

HCID 131727290HCID 131727290, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent2×

Procedure

In the Parr Hydrogenator flask with 1 mL AcOH and 10% Pd/C 0.15 g inside, 1-benzyl-3-(3-tert-butyl-diphenyl-siloxymethyl-2-fluoro-cyclobutyl)-urea in 5 mL AcOH was added. This was hydrogenolysed at 50 psi for 4 d, after which the crude mixture was filtered through celite and was purified by silica gel flash chromatography (CH2Cl2:MeOH=40:1) to give 0.15 g (63.3%, Rf=0.44 (CH2Cl2: MeOH=20:1) the desired product. IR (neat) νmax 3425, 3339, 2931, 2858, 1656, 1608, 1560, 1111, 701.

Workup

  1. filtrationafter which the crude mixture was filtered through celite
  2. customwas purified by silica gel flash chromatography (CH2Cl2:MeOH=40:1)

Sources & evidence

ORD record
ord-e1e8345fc9624bbb873618ce887eabf1
Source dataset
uspto-grants-2009_02
Patent number
US07495006B2

Reaction notes

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